Hydrochloric Acid → HCID 58529601, compound

HRID 1972787Notes

Reaction equation

HRID 1972787 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH2:27][CH2:28][CH2:29][CH2:30][O:31][Si](C(C)(C)C)(C)C)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C(O)C>[NH2:26][C:24]1[C:25]2=[C:17]([C:12]3[CH:13]=[CH:14][C:15]4[C:10]([CH:11]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:16]=4)[CH:18]=[C:19]([CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[N:20]2[N:21]=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58529505HCID 58529505, compound

Product 1

HCID 58529601HCID 58529601, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (3.00 g, 5.70 mmol) in 95% aqueous ethanol (30 mL) was added concentrated hydrochloric acid (500 μL). The reaction was stirred (rt) for 1 h. The mixture was basified (pH 8) with the addition of saturated aqueous NaHCO3 solution and was evaporated to remove volatiles. The aqueous mixture was extracted with ethyl acetate (3×25 mL) and the combined organics were washed with brine, dried (Na2SO4) and concentrated to afford 2.54 g (97%) of the desired product, which contained minor impurities. 1H NMR (300 MHz, DMSO-d6) δ 8.57 (s, 1 H), 7.91 (s, 1 H), 7.82 (d, 1 H), 7.61 (s, 1 H), 7.40-7.29 (m, 5 H), 7.17 (dd, 1 H), 6.62 (s, 1 H), 5.68 (s, 2 H), 4.43 (t, 1 H), 3.46 (q, 2 H), 2.92 (t, 2 H), 1.82-1.71 (m, 2 H), 1.60-1.50 (m, 2 H); ES-MS m/z 413.4 [M+H]+, HPLC RT (min) 2.50.

Workup

  1. customwas evaporated
  2. customto remove volatiles
  3. extractionThe aqueous mixture was extracted with ethyl acetate (3×25 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-32da3538932446c292911a684fb7a327
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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